Ammonia → Ethyl 2-acetamido-3-aminobut-2-enoate

HRID 1981642Notes

Reaction equation

HRID 1981642 reaction equation
[NH3:1].[C:2]([NH:5][CH:6]([C:12]([CH3:14])=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]>C(O)C>[C:2]([NH:5][C:6](=[C:12]([NH2:1])[CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 224840Ethyl 2-acetamido-3-oxobutanoate

Product 1

HCID 86740825Ethyl 2-acetamido-3-aminobut-2-enoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 0.054 mmol of ammonia in ethanol was added dropwise to 0.054 mol of ethyl 2-acetamidoacetoacetate in 40 ml of ice cold ethanol over a period of 10 minutes. The reaction vessel was tightly capped and allowed to stir overnight at 23° C., after which the solvent was removed at reduced pressure to provide ethyl 2-acetamido-3-aminobut-2-enoate in a 3/1 ratio of two geometrical isomers.

Workup

  1. customThe reaction vessel was tightly capped
  2. customafter which the solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-80c66047b6b5402985af6d7c529af9bf
Source dataset
uspto-grants-1986_06
Patent number
US04593118

Reaction notes

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